Bis(2-{[2-(2-hy­droxy­benzyl­amino)­eth­yl]amino­meth­yl}phenolato-κ3N,N′,O1)cobalt(III) nitrate monohydrate

Sow, M.M.; Diouf, O.; Thiam, I.E.; Gaye, M.; Retailleau, P.

doi:10.1107/S1600536811055851

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages m121-m122

doi:10.1107/S1600536811055851

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Bis(2-{[2-(2-hydroxybenzylamino)ethyl]aminomethyl}phenolato-κ³N,N′,O¹)cobalt(III) nitrate monohydrate

Mouhamadou Moustapha Sow,^a Ousmane Diouf,^a Ibrahima Elhadj Thiam,^a Mohamed Gaye ^a ^* and Pascal Retailleau ^b

^aDépartement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bICSN-CNRS, Laboratoire de Cristallochimie, 1 Avenue la Terasse, 91198 Gif-sur-Yvette, France
^*Correspondence e-mail: mlgayeastou@yahoo.fr

(Received 7 December 2011; accepted 27 December 2011; online 7 January 2012)

In the title compound, [Co(C₁₆H₁₉N₂O₂)₂]NO₃·H₂O, the Co^III ion is located on an inversion center and is six-coordinated by two phenolate O atoms and four amino N atoms from two diamine ligands, forming an octahedral geometry. The water molecule and the nitrate anion are located close to an inversion center, and are thus equally disordered by symmetry. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds involving the uncoordinated water molecule and the free phenol hydroxyl group with the nitrate anion. N—H⋯O hydrogen bonds involving the amino groups and the nitrate anions connect the complex molecules along the c axis.

Related literature

For related structures, see: Zhou (2009 ); Zhang (2010 ); Khalaji et al. (2010 ).

Experimental

Crystal data

[Co(C₁₆H₁₉N₂O₂)₂]NO₃·H₂O
M_r = 681.62
Triclinic, $[P \overline 1]$
a = 8.989 (3) Å
b = 9.032 (3) Å
c = 10.621 (4) Å
α = 106.680 (2)°
β = 99.950 (3)°
γ = 109.720 (2)°
V = 742.0 (4) Å³
Z = 1
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 293 K
0.42 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.640, T_max = 0.930
16124 measured reflections
2694 independent reflections
2303 reflections with I > 2σigma(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.10
2689 reflections
234 parameters
29 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—O1	1.896 (2)
Co1—N1	1.950 (2)
Co1—N2	1.997 (2)
Symmetry code: (i) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O21—H21O⋯O12ⁱⁱ	0.95	2.27	3.025 (12)	136
O21—H22O⋯O13ⁱⁱ	0.95	2.18	2.922 (13)	134
O2—H2O⋯O21ⁱⁱⁱ	0.82	1.99	2.787 (9)	165
O2—H2O⋯O11ⁱⁱⁱ	0.82	2.01	2.823 (9)	169
N1—H1N⋯O12^iv	0.86	2.35	3.185 (10)	165
N1—H1N⋯O13ⁱ	0.86	2.31	3.145 (11)	163
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z; (iii) x-1, y-1, z; (iv) x, y, z+1.

Data collection: COLLECT (Nonius, 1998 ) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055851/bh2406sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055851/bh2406Isup2.hkl

checkCIF report

Comment top

Schiff bases with N₂O₂ inners have been used to synthesize complexes, due to their chelating ability for metal atoms. In this paper, the title new cobalt(III) complex with the diamine ligand [2-((2-hydroxybenzylamino)ethylamino)methyl]phenol, is reported. The Co^III ion is six-coordinated by four amino N atoms and two phenolate O atoms from two ligands, forming an octahedral geometry (Fig. 1). The ligands present one of the hydroxyl groups protonated while the coordinated one is deprotonated. The equatorial sites are occupied by two amino N atoms and two phenolate O atoms from the same arm of the ligand and the two axial sites are occupied by the amino N atoms owned by the arm bearing the non deprotonated phenol group. The Co—O and Co—N equatorial bond lengths are 1.896 (2) and 1.950 (2) Å, while Co—N axial bond lengths is 1.997 (2) Å (Table 1). They are comparable to the bond lengths in similar octahedral cobalt complexes (Zhou, 2009; Zhang, 2010; Khalaji et al., 2010). The NO₃^- ion and the lattice water molecule are disordered over two sets of sites, with relative occupancies of 0.5 for each group. In the crystal structure, the molecules of the compound are linked into a three-dimensional framework by a combination of O—H···O, N—H···O, and C—H···π(arene) hydrogen bonds and also π–π stacking interactions. The first hydrogen bond type utilizes hydroxyl atoms O2 as donors to link the Co complexes through either a water molecule or a nitrate ion (the water molecule being H-bonded to the nitrate ion over a crystallographic inversion center) into an infinite chain along the [221] direction. Benzyl ring at general position form π–π interactions with its neighbor at (1 - x, 1 - y, 1 - z), with distance between ring centroids of 3.534 (3) Å. This pair is further sandwiched by C—H···π(arene) hydrogen bond developed by atom C9 with H9B···Cg distance of 2.76 Å, and X—H ··· Cg angle of 145°, and even more weakly by the edge of the phenolic group. These aromatic interactions interspersed by the solvent molecules but propagating along the [231] direction combine with the previous linear H-bond chain to form a molecular sheet lying parallel to (-102) (Fig. 2). Orthogonally to the sheet, the third dimensionality is developed by an hydrogen bond between the amine atom N1 and the nitrate ion, along the c axis.

Related literature top

For related structures, see: Zhou (2009); Zhang (2010); Khalaji et al. (2010).

Experimental top

Diethylenetriamine (1.0311 g, 10 mmol) and salicylaldehyde (2.4408 g, 20 mmol) were dissolved in 20 ml of ethanol with few drops of glacial acetic acid. The mixture was refluxed for 3 h. On cooling, a yellow oil was isolated. To 20 ml of anhydrous methanol was added the yellow oil (1.5 g, 5.59 mmol). The mixture was cooled to 273 K before NaBH₄ (0.63 g, 16.7 mmol) was added in small portions. A white precipitate was isolated after 30 mn of stirring by filtration. In a round-bottom flask, 15 ml of methanol and the prepared ligand (0.2 g, 0.735 mmol) were mixed. Cobalt nitrate hexahydrate (0.21, 0.735 mmol) dissolved in 5 ml of methanol was introduced. Immediate color change was observed, indicating instant occurrence of the formation of the complex. The mixture was stirred at room temperature for 2 h. The brown solution was filtered off and the filtrate was left at room temperature. After two weeks, brown crystals suitable for X-ray analyses were obtained. Yield: 75%. Anal. Calc. for [C₃₂H₄₀N₅O₈Co]: C 56.39, H 5.91, N 10.27%. Found: C 56.38, H 5.93, N 10.28%. Selected IR data (cm^-1, KBr pellet): 400, 3216, 1600, 1582, 1458, 764.

Computing details top

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP view of the title compound, showing displacement ellipsoids at the 50% probability level. [Symmetry operator a: -x + 1, -y, -z + 1]. A single position for nitrate and water groups has been retained.
	Fig. 2. Molecular representation of the compound showing hydrogen bonds. Broken lines stand for hydrogen bonds.

Bis(2-{[2-(2-hydroxybenzylamino)ethyl]aminomethyl}phenolato- κ³N,N',O¹)cobalt(III) nitrate monohydrate top

Crystal data top

[Co(C₁₆H₁₉N₂O₂)₂]NO₃·H₂O	Z = 1
M_r = 681.62	F(000) = 358
Triclinic, P1	D_x = 1.525 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 8.989 (3) Å	Cell parameters from 2525 reflections
b = 9.032 (3) Å	θ = 0.4–25.4°
c = 10.621 (4) Å	µ = 0.64 mm⁻¹
α = 106.680 (2)°	T = 293 K
β = 99.950 (3)°	Parallelepipedic stick, brown
γ = 109.720 (2)°	0.42 × 0.14 × 0.12 mm
V = 742.0 (4) Å³

Data collection top

Nonius KappaCCD diffractometer	2694 independent reflections
Radiation source: fine-focus sealed tube	2303 reflections with I > 2σigma(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.019
Detector resolution: 9 pixels mm^-1	θ_max = 25.7°, θ_min = 2.8°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −10→10
T_min = 0.640, T_max = 0.930	l = −12→12
16124 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0583P)² + 0.3846P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2689 reflections	Δρ_max = 0.25 e Å⁻³
234 parameters	Δρ_min = −0.48 e Å⁻³
29 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.058 (9)
Primary atom site location: structure-invariant direct methods

Crystal data top

[Co(C₁₆H₁₉N₂O₂)₂]NO₃·H₂O	γ = 109.720 (2)°
M_r = 681.62	V = 742.0 (4) Å³
Triclinic, P1	Z = 1
a = 8.989 (3) Å	Mo Kα radiation
b = 9.032 (3) Å	µ = 0.64 mm⁻¹
c = 10.621 (4) Å	T = 293 K
α = 106.680 (2)°	0.42 × 0.14 × 0.12 mm
β = 99.950 (3)°

Data collection top

Nonius KappaCCD diffractometer	2694 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2303 reflections with I > 2σigma(I)
T_min = 0.640, T_max = 0.930	R_int = 0.019
16124 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	29 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.10	Δρ_max = 0.25 e Å⁻³
2689 reflections	Δρ_min = −0.48 e Å⁻³
234 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.5000	0.0000	0.5000	0.0525 (2)
O1	0.5163 (2)	0.1737 (3)	0.4297 (2)	0.0576 (5)
O2	−0.0155 (3)	−0.4955 (3)	0.1901 (3)	0.0811 (7)
H2O	−0.0938	−0.5812	0.1814	0.122*
N1	0.4113 (3)	0.0896 (3)	0.6449 (2)	0.0568 (6)
H1N	0.4568	0.0862	0.7215	0.068*
N2	0.2647 (3)	−0.1449 (3)	0.3863 (2)	0.0568 (6)
H2N	0.2543	−0.2386	0.3935	0.068*
C1	0.4130 (3)	0.2510 (4)	0.4369 (3)	0.0572 (7)
C2	0.3471 (4)	0.2816 (4)	0.3232 (3)	0.0631 (7)
H2	0.3774	0.2503	0.2435	0.076*
C3	0.2380 (4)	0.3575 (4)	0.3273 (4)	0.0705 (8)
H3	0.1945	0.3762	0.2502	0.085*
C4	0.1928 (4)	0.4059 (4)	0.4441 (4)	0.0735 (9)
H4	0.1179	0.4561	0.4461	0.088*
C5	0.2590 (4)	0.3796 (4)	0.5582 (4)	0.0700 (8)
H5	0.2302	0.4149	0.6381	0.084*
C6	0.3679 (4)	0.3016 (4)	0.5563 (3)	0.0602 (7)
C7	0.4394 (4)	0.2700 (4)	0.6785 (3)	0.0649 (8)
H7A	0.5575	0.3400	0.7142	0.078*
H7B	0.3898	0.3029	0.7501	0.078*
C8	0.2337 (3)	−0.0254 (4)	0.6089 (3)	0.0646 (8)
H8A	0.1770	0.0346	0.6580	0.077*
H8B	0.2245	−0.1213	0.6358	0.077*
C9	0.1554 (3)	−0.0863 (4)	0.4564 (3)	0.0632 (8)
H9A	0.0471	−0.1785	0.4286	0.076*
H9B	0.1419	0.0050	0.4320	0.076*
C10	0.2197 (3)	−0.1723 (4)	0.2372 (3)	0.0650 (8)
H10A	0.2601	−0.2527	0.1904	0.078*
H10B	0.2779	−0.0659	0.2277	0.078*
C11	0.0387 (3)	−0.2355 (4)	0.1642 (3)	0.0593 (7)
C12	−0.0188 (4)	−0.1310 (4)	0.1179 (3)	0.0673 (8)
H12	0.0539	−0.0202	0.1376	0.081*
C13	−0.1816 (4)	−0.1876 (5)	0.0434 (3)	0.0698 (8)
H13	−0.2187	−0.1153	0.0138	0.084*
C14	−0.2878 (4)	−0.3500 (4)	0.0135 (3)	0.0670 (8)
H14	−0.3973	−0.3893	−0.0388	0.080*
C15	−0.2359 (4)	−0.4569 (4)	0.0591 (3)	0.0644 (8)
H15	−0.3095	−0.5679	0.0380	0.077*
C16	−0.0727 (4)	−0.3981 (4)	0.1370 (3)	0.0602 (7)
O11	0.7320 (11)	0.1846 (10)	0.1338 (9)	0.123 (3)	0.50
N11	0.5877 (7)	0.0882 (8)	0.0550 (6)	0.0742 (14)	0.50
O12	0.5389 (14)	0.1116 (12)	−0.0485 (10)	0.104 (3)	0.50
O13	0.5023 (13)	−0.0330 (11)	0.0776 (11)	0.097 (3)	0.50
O21	0.7119 (11)	0.2509 (10)	0.2025 (9)	0.111 (3)	0.50
H21O	0.6490	0.1443	0.2054	0.167*	0.50
H22O	0.6628	0.2429	0.1127	0.167*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0430 (3)	0.0580 (4)	0.0498 (3)	0.0179 (2)	0.0079 (2)	0.0177 (2)
O1	0.0520 (11)	0.0630 (12)	0.0589 (11)	0.0241 (9)	0.0139 (8)	0.0252 (9)
O2	0.0661 (14)	0.0758 (16)	0.0986 (18)	0.0311 (12)	0.0078 (13)	0.0361 (14)
N1	0.0479 (12)	0.0637 (15)	0.0515 (13)	0.0188 (11)	0.0079 (10)	0.0201 (11)
N2	0.0479 (12)	0.0655 (15)	0.0518 (13)	0.0213 (11)	0.0100 (10)	0.0201 (11)
C1	0.0450 (14)	0.0562 (16)	0.0628 (17)	0.0167 (12)	0.0093 (12)	0.0204 (13)
C2	0.0539 (16)	0.0654 (19)	0.0664 (18)	0.0210 (14)	0.0105 (13)	0.0281 (15)
C3	0.0584 (18)	0.073 (2)	0.080 (2)	0.0257 (16)	0.0103 (15)	0.0351 (17)
C4	0.0567 (18)	0.072 (2)	0.095 (3)	0.0299 (16)	0.0163 (17)	0.0352 (18)
C5	0.0600 (18)	0.0657 (19)	0.078 (2)	0.0246 (15)	0.0203 (15)	0.0201 (16)
C6	0.0527 (15)	0.0572 (17)	0.0623 (17)	0.0197 (13)	0.0107 (13)	0.0179 (13)
C7	0.0602 (17)	0.069 (2)	0.0585 (17)	0.0270 (15)	0.0133 (13)	0.0152 (14)
C8	0.0470 (15)	0.081 (2)	0.0590 (17)	0.0194 (14)	0.0154 (12)	0.0248 (15)
C9	0.0418 (14)	0.076 (2)	0.0610 (17)	0.0170 (13)	0.0119 (12)	0.0208 (15)
C10	0.0478 (15)	0.080 (2)	0.0512 (16)	0.0180 (14)	0.0062 (12)	0.0179 (14)
C11	0.0480 (15)	0.0691 (19)	0.0486 (15)	0.0186 (14)	0.0071 (11)	0.0158 (13)
C12	0.0589 (17)	0.070 (2)	0.0611 (18)	0.0168 (15)	0.0104 (14)	0.0232 (15)
C13	0.0622 (18)	0.080 (2)	0.0670 (19)	0.0297 (17)	0.0109 (15)	0.0320 (17)
C14	0.0483 (15)	0.087 (2)	0.0565 (17)	0.0240 (16)	0.0074 (13)	0.0230 (16)
C15	0.0514 (16)	0.0666 (19)	0.0599 (17)	0.0169 (14)	0.0086 (13)	0.0155 (14)
C16	0.0531 (16)	0.0650 (18)	0.0565 (16)	0.0243 (14)	0.0101 (12)	0.0178 (14)
O11	0.129 (6)	0.083 (5)	0.122 (7)	0.026 (4)	−0.011 (5)	0.041 (5)
N11	0.070 (3)	0.073 (4)	0.079 (4)	0.027 (3)	0.021 (3)	0.032 (3)
O12	0.113 (7)	0.107 (7)	0.078 (5)	0.028 (6)	0.011 (4)	0.044 (5)
O13	0.094 (5)	0.089 (6)	0.090 (5)	0.012 (4)	0.018 (4)	0.042 (5)
O21	0.100 (5)	0.081 (5)	0.134 (7)	0.017 (4)	0.016 (5)	0.050 (5)

Geometric parameters (Å, º) top

Co1—O1ⁱ	1.896 (2)	N11—O13	1.222 (9)
Co1—O1	1.896 (2)	N11—O13ⁱⁱ	1.348 (12)
Co1—N1ⁱ	1.950 (2)	N11—N11ⁱⁱ	1.728 (12)
Co1—N1	1.950 (2)	N11—O12ⁱⁱ	1.753 (10)
Co1—N2ⁱ	1.997 (2)	O12—O13ⁱⁱ	0.627 (11)
Co1—N2	1.997 (2)	O12—N11ⁱⁱ	1.753 (10)
O1—C1	1.337 (3)	O13—O12ⁱⁱ	0.627 (11)
O2—C16	1.358 (4)	O13—N11ⁱⁱ	1.348 (12)
N1—C7	1.484 (4)	O2—H2O	0.8200
N1—C8	1.488 (4)	N1—H1N	0.8595
N2—C9	1.475 (4)	N2—H2N	0.8468
N2—C10	1.490 (4)	C2—H2	0.9300
C1—C2	1.393 (4)	C3—H3	0.9300
C1—C6	1.397 (4)	C4—H4	0.9300
C2—C3	1.373 (4)	C5—H5	0.9300
C3—C4	1.370 (5)	C7—H7A	0.9700
C4—C5	1.375 (5)	C7—H7B	0.9700
C5—C6	1.385 (4)	C8—H8A	0.9700
C6—C7	1.493 (4)	C8—H8B	0.9700
C8—C9	1.502 (4)	C9—H9A	0.9700
C10—C11	1.502 (4)	C9—H9B	0.9700
C11—C12	1.381 (4)	C10—H10A	0.9700
C11—C16	1.381 (4)	C10—H10B	0.9700
C12—C13	1.375 (4)	C12—H12	0.9300
C13—C14	1.359 (5)	C13—H13	0.9300
C14—C15	1.371 (5)	C14—H14	0.9300
C15—C16	1.386 (4)	C15—H15	0.9300
O11—N11	1.259 (9)	O21—H21O	0.9503
N11—O12	1.214 (11)	O21—H22O	0.9504

O1ⁱ—Co1—O1	180	O12—N11—O11	118.7 (8)
O1ⁱ—Co1—N1ⁱ	94.28 (10)	O13—N11—O11	120.6 (8)
O1—Co1—N1ⁱ	85.72 (10)	C16—O2—H2O	109.5
O1ⁱ—Co1—N1	85.72 (9)	C7—N1—H1N	104.3
O1—Co1—N1	94.28 (10)	C8—N1—H1N	104.2
N1ⁱ—Co1—N1	180	Co1—N1—H1N	111.3
O1ⁱ—Co1—N2ⁱ	93.87 (9)	C9—N2—H2N	107.1
O1—Co1—N2ⁱ	86.13 (9)	C10—N2—H2N	108.3
N1ⁱ—Co1—N2ⁱ	86.32 (10)	Co1—N2—H2N	100.6
N1—Co1—N2ⁱ	93.68 (9)	C3—C2—H2	119.6
O1ⁱ—Co1—N2	86.13 (9)	C1—C2—H2	119.6
O1—Co1—N2	93.87 (9)	C4—C3—H3	119.8
N1ⁱ—Co1—N2	93.68 (9)	C2—C3—H3	119.8
N1—Co1—N2	86.32 (10)	C3—C4—H4	120.3
N2ⁱ—Co1—N2	180	C5—C4—H4	120.3
C1—O1—Co1	122.22 (18)	C4—C5—H5	119.4
C7—N1—C8	113.1 (2)	C6—C5—H5	119.4
C7—N1—Co1	114.85 (19)	N1—C7—H7A	109.1
C8—N1—Co1	108.49 (18)	C6—C7—H7A	109.1
C9—N2—C10	112.6 (2)	N1—C7—H7B	109.1
C9—N2—Co1	109.04 (17)	C6—C7—H7B	109.1
C10—N2—Co1	117.92 (18)	H7A—C7—H7B	107.9
O1—C1—C2	119.8 (3)	N1—C8—H8A	109.8
O1—C1—C6	121.5 (3)	C9—C8—H8A	109.8
C2—C1—C6	118.6 (3)	N1—C8—H8B	109.8
C3—C2—C1	120.8 (3)	C9—C8—H8B	109.8
C4—C3—C2	120.5 (3)	H8A—C8—H8B	108.3
C3—C4—C5	119.5 (3)	N2—C9—H9A	110.1
C4—C5—C6	121.2 (3)	C8—C9—H9A	110.1
C5—C6—C1	119.4 (3)	N2—C9—H9B	110.1
C5—C6—C7	122.0 (3)	C8—C9—H9B	110.1
C1—C6—C7	118.7 (3)	H9A—C9—H9B	108.4
N1—C7—C6	112.3 (2)	N2—C10—H10A	108.2
N1—C8—C9	109.2 (2)	C11—C10—H10A	108.2
N2—C9—C8	108.0 (2)	N2—C10—H10B	108.2
N2—C10—C11	116.5 (2)	C11—C10—H10B	108.2
C12—C11—C16	118.2 (3)	H10A—C10—H10B	107.3
C12—C11—C10	119.6 (3)	C13—C12—H12	119.3
C16—C11—C10	122.1 (3)	C11—C12—H12	119.3
C13—C12—C11	121.3 (3)	C14—C13—H13	120.3
C14—C13—C12	119.4 (3)	C12—C13—H13	120.3
C13—C14—C15	121.0 (3)	C13—C14—H14	119.5
C14—C15—C16	119.4 (3)	C15—C14—H14	119.5
O2—C16—C11	117.3 (3)	C14—C15—H15	120.3
O2—C16—C15	122.2 (3)	C16—C15—H15	120.3
C11—C16—C15	120.6 (3)	H21O—O21—H22O	104.1
O12—N11—O13	120.6 (8)

N1ⁱ—Co1—O1—C1	149.8 (2)	C7—N1—C8—C9	90.2 (3)
N1—Co1—O1—C1	−30.2 (2)	Co1—N1—C8—C9	−38.5 (3)
N2ⁱ—Co1—O1—C1	−123.6 (2)	C10—N2—C9—C8	−167.3 (3)
N2—Co1—O1—C1	56.4 (2)	Co1—N2—C9—C8	−34.4 (3)
O1ⁱ—Co1—N1—C7	161.25 (19)	N1—C8—C9—N2	48.1 (3)
O1—Co1—N1—C7	−18.75 (19)	C9—N2—C10—C11	−33.9 (4)
N2ⁱ—Co1—N1—C7	67.64 (19)	Co1—N2—C10—C11	−162.3 (2)
N2—Co1—N1—C7	−112.36 (19)	N2—C10—C11—C12	112.2 (3)
O1ⁱ—Co1—N1—C8	−71.16 (19)	N2—C10—C11—C16	−70.1 (4)
O1—Co1—N1—C8	108.84 (19)	C16—C11—C12—C13	−1.8 (5)
N2ⁱ—Co1—N1—C8	−164.77 (19)	C10—C11—C12—C13	176.0 (3)
N2—Co1—N1—C8	15.23 (19)	C11—C12—C13—C14	−0.7 (5)
O1ⁱ—Co1—N2—C9	96.9 (2)	C12—C13—C14—C15	1.5 (5)
O1—Co1—N2—C9	−83.1 (2)	C13—C14—C15—C16	0.0 (5)
N1ⁱ—Co1—N2—C9	−169.1 (2)	C12—C11—C16—O2	−176.4 (3)
N1—Co1—N2—C9	10.9 (2)	C10—C11—C16—O2	5.8 (4)
O1ⁱ—Co1—N2—C10	−133.0 (2)	C12—C11—C16—C15	3.4 (4)
O1—Co1—N2—C10	47.0 (2)	C10—C11—C16—C15	−174.4 (3)
N1ⁱ—Co1—N2—C10	−39.0 (2)	C14—C15—C16—O2	177.2 (3)
N1—Co1—N2—C10	141.0 (2)	C14—C15—C16—C11	−2.5 (5)
Co1—O1—C1—C2	−136.5 (2)	O13—N11—O12—O13ⁱⁱ	−29 (3)
Co1—O1—C1—C6	43.1 (3)	O11—N11—O12—O13ⁱⁱ	147 (2)
O1—C1—C2—C3	178.6 (3)	N11ⁱⁱ—N11—O12—O13ⁱⁱ	−18 (2)
C6—C1—C2—C3	−1.0 (5)	O12ⁱⁱ—N11—O12—O13ⁱⁱ	−18 (2)
C1—C2—C3—C4	0.5 (5)	O13—N11—O12—N11ⁱⁱ	−10.6 (13)
C2—C3—C4—C5	0.7 (5)	O11—N11—O12—N11ⁱⁱ	164.8 (9)
C3—C4—C5—C6	−1.5 (5)	O13ⁱⁱ—N11—O12—N11ⁱⁱ	18 (2)
C4—C5—C6—C1	0.9 (5)	O12ⁱⁱ—N11—O12—N11ⁱⁱ	0.0
C4—C5—C6—C7	−179.2 (3)	O12—N11—O13—O12ⁱⁱ	49 (5)
O1—C1—C6—C5	−179.3 (3)	O11—N11—O13—O12ⁱⁱ	−127 (4)
C2—C1—C6—C5	0.3 (4)	O13ⁱⁱ—N11—O13—O12ⁱⁱ	36 (4)
O1—C1—C6—C7	0.8 (4)	N11ⁱⁱ—N11—O13—O12ⁱⁱ	36 (4)
C2—C1—C6—C7	−179.6 (3)	O12—N11—O13—N11ⁱⁱ	12.9 (16)
C8—N1—C7—C6	−67.3 (3)	O11—N11—O13—N11ⁱⁱ	−162.4 (9)
Co1—N1—C7—C6	57.9 (3)	O13ⁱⁱ—N11—O13—N11ⁱⁱ	0.0
C5—C6—C7—N1	126.1 (3)	O12ⁱⁱ—N11—O13—N11ⁱⁱ	−36 (4)
C1—C6—C7—N1	−54.0 (4)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21O···O12ⁱⁱ	0.95	2.27	3.025 (12)	136
O21—H22O···O13ⁱⁱ	0.95	2.18	2.922 (13)	134
O2—H2O···O21ⁱⁱⁱ	0.82	1.99	2.787 (9)	165
O2—H2O···O11ⁱⁱⁱ	0.82	2.01	2.823 (9)	169
N1—H1N···O12^iv	0.86	2.35	3.185 (10)	165
N1—H1N···O13ⁱ	0.86	2.31	3.145 (11)	163

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) x−1, y−1, z; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₁₆H₁₉N₂O₂)₂]NO₃·H₂O
M_r	681.62
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.989 (3), 9.032 (3), 10.621 (4)
α, β, γ (°)	106.680 (2), 99.950 (3), 109.720 (2)
V (Å³)	742.0 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.42 × 0.14 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.640, 0.930
No. of measured, independent and observed [I > 2σigma(I)] reflections	16124, 2694, 2303
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.10
No. of reflections	2689
No. of parameters	234
No. of restraints	29
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.48

Computer programs: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and CRYSTALBUILDER (Welter, 2006), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—O1	1.896 (2)	Co1—N2	1.997 (2)
Co1—N1	1.950 (2)

O1ⁱ—Co1—O1	180	O1—Co1—N2	93.87 (9)
O1—Co1—N1ⁱ	85.72 (10)	N1ⁱ—Co1—N2	93.68 (9)
O1—Co1—N1	94.28 (10)	N1—Co1—N2	86.32 (10)
N1ⁱ—Co1—N1	180	N2ⁱ—Co1—N2	180
O1ⁱ—Co1—N2	86.13 (9)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21O···O12ⁱⁱ	0.95	2.27	3.025 (12)	135.8
O21—H22O···O13ⁱⁱ	0.95	2.18	2.922 (13)	134.2
O2—H2O···O21ⁱⁱⁱ	0.82	1.99	2.787 (9)	165.4
O2—H2O···O11ⁱⁱⁱ	0.82	2.01	2.823 (9)	168.7
N1—H1N···O12^iv	0.86	2.35	3.185 (10)	165.3
N1—H1N···O13ⁱ	0.86	2.31	3.145 (11)	162.9

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) x−1, y−1, z; (iv) x, y, z+1.

Acknowledgements

The authors thank Professor Amadou Tidiane, BA Minister of Higher Education of Senegal, for his financial support.

References

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